When to quit

How do you know when to quit?

I think one of the keys is self-awareness. The impulse to quit or persist is usually emotional and not analytical; if you look at your past track record you can tell if you tend to quit too early or too late, and adjust your behaviour accordingly.

I’m terrible at sticking with things—at the first sign of trouble I usually throw in the towel and start doing something else. Of course, that’s not the story I tell myself—it’s always something about opportunity cost, working smarter, not harder, etc—when, in fact, it’s probably just disguised laziness and fear of failure. However, I’m old enough to have figured out that this is how I work; knowing that I’m biased in favour of quitting, I should be skeptical of the impulse to quit and not follow it blindly.

However, I think there is another lens from which you can view quitting. Considering things that you can quit, I think it’s useful to split them up into three categories:

• Goals: High-level goals of what you want to accomplish in life, e.g. the person you want to be, the relationships you wish to have, the career you want to pursue, etc.
• Strategies: Ways in which you can reach your goal
• Tactics: The concrete steps you take as part of your strategy

As an example, let’s say that you want to be a professional author—broken down into these categories, that would be:

• Goal: Become a professional author
• Strategy: Publish a novel
• Tactic: Practice and build an audience by writing short stories

The higher up you get in your list the more you should persist and stick to your goals. For example, there’s no reason to believe that anyone couldn’t work as a professional author as long as they apply themselves. Everyone can’t be churning out best-sellers, but it shouldn’t be controversial to say it’s within everyone’s reach to e.g. make a living writing for a local newspaper.

Put another way, the decision to quit your high-level goal would be purely emotional. Tactics, on the other hand, should carry zero emotional attachment. You should quit them as soon as you discover that they don’t seem to work. The important part here is that you need to actually try them out to test if they’re taking you in the right direction—you need to solicit feedback from the universe. You don’t want to be in a position where you’ve written a 1000-page manuscript for a fantasy epic, only to discover that no-one wants to read it. Make incremental, small bets—do more of the ones that work and stop doing the ones that don’t.

I think strategies are what trips most people up. A strategy is a long-term commitment that is not guaranteed to work out. This makes it tempting to give up and search for something that will yield an “easy win” instead—but most of the time, there are no easy wins, and switching is just done in vain.

Good tactics help—if you’re making many small bets you can gauge whether they seem to be taking you in the right direction. However, rewards and other positive signals might still take long to arrive. I think this is where self-awareness is important—are you the kind of person who has a hard time with commitment in general? Are you a serial quitter? In that case, you should probably ignore your gut and just press on.

Ask yourself:

• Did you really give this thing a fair shake?
• What assumptions did you have going in? Are they still true, or did something change?
• Are you considering quitting as a result of thorough analysis, or is it just an impulse?

It feels like strategies are kind of like relationships—there is an initial honeymoon phase, where everything seems perfect and effortless. Then reality hits, and you realize that things might not be as easy as they first seemed. However, the real rewards often come once you persist through this phase—imagine if Columbus had turned around when he was halfway across the Atlantic.

Again, a strategy is a commitment—make sure you honor it and give it your best shot before you consider moving on.